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Synlett 2008(17): 2617-2620  
DOI: 10.1055/s-0028-1083511
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Synthesis of Leustroducsin B

Joëlle Moïsea, Ravindra P. Sonawanea, Camilla Corsib, Sebastian V. Wendebornb, Stellios Arseniyadis*a, Janine Cossy*a
a Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS, 10 Rue Vauquelin, 75231 Paris Cedex 05, France
Fax: +33(1)40794660; e-Mail: stellios.arseniyadis@espci.fr; e-Mail: janine.cossy@espci.fr;
b Syngenta Crop Protection Muenchwilen AG, WST-820.2.15, Schaffhauserstr. 4332 Stein, Switzerland
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Publikationsverlauf

Received 2 July 2008
Publikationsdatum:
01. Oktober 2008 (online)

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Abstract

A formal synthesis of leustroducsin B, a potent antitumor compound, is described featuring two key reactions: an olefin cross-metathesis between α-methylene γ-butyrolactone and a terminal olefin to install the C7-C12 carbon backbone, and a highly stereoselective Brown-type pentenylation which sets the syn-relationship between the two substituents at C4 and C5.

Key words

leustroducsins - antitumor - asymmetric pentenylation - ring-closing metathesis - Sharpless dihydroxylation

    References and Notes

  • 1a Kohama T. Enokita R. Okazaki T. Miyaoka H. Torikata A. Inukai M. Kaneko I. Kagasaki T. Sakaida Y. Satoh A. Shiraishi A. J. Antibiot.  1993,  46:  1503 
    Google Scholar
  • 1b Kohama T. Nakamura T. Kinoshita T. Kaneko I. Shiraishi A. J. Antibiot.  1993,  46:  1512 
    Google Scholar
  • 1c Matsuhashi H. Shimada K. Tetrahedron  2002,  58:  5619 
    Google Scholar
  • 2a Fushimi S. Nishikawa S. Shimazu A. Seto H. J. Antibiot.  1989,  42:  1019 
    Google Scholar
  • 2b Fushimi S. Furihata K. Seto H. J. Antibiot.  1989,  42:  1026 
    Google Scholar
  • 2c Ozasa T. Suzuki K. Sasamata M. Tanaka K. Kobori M. Kadota S. Nagai K. Saito T. Watanabe S. Iwanami M. J. Antibiot.  1989,  42:  1331 
    Google Scholar
  • 2d Ozasa T. Tanaka K. Sasamata M. Kaniwa H. Shimizu M. Matsumoto H. Iwanami M. J. Antibiot.  1989,  42:  1339 
    Google Scholar
  • 2e Shibata T. Kurihara S. Yoda K. Haruyama H. Tetrahedron  1995,  51:  11999 
    Google Scholar
  • 2f Sekiyama Y. Palaniappan N. Reynolds KA. Osada H. Tetrahedron  2003,  59:  7465 
    Google Scholar
  • 2g Choudhuri SD. Ayers S. Soine WH. Reynolds KA. J. Antibiot.  2005,  58:  573 
    Google Scholar
  • 2h Mizuhara N. Usuki Y. Ogita M. Fujita K. Kuroda M. Doe M. Lio H. Tanaka T. J. Antibiot.  2007,  60:  762 
    Google Scholar
  • 2i Nonaka H. Maeda N. Kobayashi Y. Tetrahedron Lett.  2007,  48:  5601 ; and references therein
    Google Scholar
  • 3a Lewy DS. Gauss CM. Soenen DR. Boger DL. Curr. Med. Chem.  2002,  9:  2005 
    Google Scholar
  • 3b Uramoto M. Shen YC. Takizawa N. Kusakabe H. Isono K. J. Antibiot.  1985,  38:  665 
    Google Scholar
  • 4 Kawada M. Kawatsu M. Masuda T. Ohba S. Amemiya M. Kohama T. Ishizuka M. Takeuchi T. Int. Immunopharmacol.  2003,  3:  179 
    CrossrefGoogle Scholar
  • 5 Koishi R. Yoshimura C. Kohama T. Serizawa N.
    J. Interferon Cytokine Res.  2002,  22:  343 
    CrossrefGoogle Scholar
  • 6 Shimada K. Kaburagi Y. Fukuyama T. J. Am. Chem. Soc.  2003,  125:  4048 
    CrossrefGoogle Scholar
  • 7a Miyashita K. Tsunemi T. Hosokawa T. Ikejiri M. Imanishi T. Tetrahedron Lett.  2007,  48:  3829 
    Google Scholar
  • 7b Miyashita K. Tsunemi T. Hosokawa T. Ikejiri M. Imanishi T. J. Org. Chem.  2008,  73:  5360 
    Google Scholar
  • 8 Hatakeyama et al. have very recently disclosed a similar procedure in their synthesis of phoslactomycin B, see: Shibahara S. Fujino M. Tashiro Y. Takahashi K. Ishihara J. Hatakeyama S. Org. Lett.  2008,  10:  2139 
    CrossrefGoogle Scholar
  • 9a Pospísil J. Markó IE. Tetrahedron Lett.  2006,  47:  5933 
    Google Scholar
  • 9b Enders D. Lenzen A. Müller M. Synthesis  2004,  1486 
    Google Scholar
  • 10 Moïse J. Arseniyadis S. Cossy J. Org. Lett.  2007,  9:  1695 
    CrossrefGoogle Scholar
  • 11 Brown HC. Bhat KS. J. Am. Chem. Soc.  1986,  108:  293 
    CrossrefGoogle Scholar
  • 13 Stork G. Zhao K. Tetrahedron Lett.  1989,  30:  2173 
    CrossrefGoogle Scholar
12

The second diastereomer could not be detected by either ¹H or ¹³C NMR spectroscopy of the crude reaction mixture, thus suggesting a selectivity superior to 95:5.